{2-[3-(4-{4-[Bis-(2-chloro-ethyl)-amino]-phenyl}-butyrylamino)-propoxy]-1,1-bis-[3-(4-{4-[bis-(2-chloro-ethyl)-amino]-phenyl}-butyrylamino)-propoxymethyl]-ethyl}-carbamic acid benzyl ester | 510753-81-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: {2-[3-(4-{4-[Bis-(2-chloro-ethyl)-amino]-phenyl}-butyrylamino)-propoxy]-1,1-bis-[3-(4-{4-[bis-(2-chloro-ethyl)-amino]-phenyl}-butyrylamino)-propoxymethyl]-ethyl}-carbamic acid benzyl ester
• 英文别名: benzyl N-[1,3-bis[3-[4-[4-[bis(2-chloroethyl)amino]phenyl]butanoylamino]propoxy]-2-[3-[4-[4-[bis(2-chloroethyl)amino]phenyl]butanoylamino]propoxymethyl]propan-2-yl]carbamate
• CAS: 510753-81-8
• 化学式: C₆₃H₈₉Cl₆N₇O₈
• 分子量: 1285.16
• InChiKey: FIAOOSTYSPTMCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  84
• 可旋转键数：
  49
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  163
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  {2-[3-(4-{4-[Bis-(2-chloro-ethyl)-amino]-phenyl}-butyrylamino)-propoxy]-1,1-bis-[3-(4-{4-[bis-(2-chloro-ethyl)-amino]-phenyl}-butyrylamino)-propoxymethyl]-ethyl}-carbamic acid benzyl ester 在 palladium on activated charcoal N-甲基吗啉 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.75h， 生成 4-[4-[bis(2-chloroethyl)amino]phenyl]-N-[3-[3-[3-[4-[4-[bis(2-chloroethyl)amino]phenyl]butanoylamino]propoxy]-2-[3-[4-[4-[bis(2-chloroethyl)amino]phenyl]butanoylamino]propoxymethyl]-2-[3-(2,5-dioxopyrrol-1-yl)propanoylamino]propoxy]propyl]butanamide
  参考文献：
  名称：

  Enabling ScFvs as multi-drug carriers: A dendritic approach

  摘要：

  To enable scFvs as multi-drug carriers, we designed and synthesized dendritic linker molecules bearing up to nine chlorambucil residues at the branch ends. A maleimide group was used at the focal point of the dendron for easy linkage to the scFv. Originally designed molecules showed poor water solubility. To address this problem, a lysine residue with an unprotected carboxylic acid group was inserted into the dendron branches. The new molecules showed excellent water solubility and are now suitable for conjugation. Such dendritic molecules will allow studies to understand the relationship between the drug/antibody ratio and the potency of the immunoconjugates. The dendritic approach could also be applied to drugs other than chlorambucil and carriers other than scFvs to greatly increase the drug/carrier ratio. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00057-9
• 作为产物：
  描述：

  tris(cyanoethoxymethyl)aminomethane 在 N-甲基吗啉 、 sodium tetrahydroborate 、 碳酸氢钠 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 cobalt(II) chloride 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 {2-[3-(4-{4-[Bis-(2-chloro-ethyl)-amino]-phenyl}-butyrylamino)-propoxy]-1,1-bis-[3-(4-{4-[bis-(2-chloro-ethyl)-amino]-phenyl}-butyrylamino)-propoxymethyl]-ethyl}-carbamic acid benzyl ester
  参考文献：
  名称：

  Syntheses of dendritic linkers containing chlorambucil residues for the preparation of antibody–multidrug immunoconjugates

  摘要：

  A novel dendritic molecule with nine chlorambucil (CBL) residues on the surface and a maleimide moiety at the core terminus was synthesized using a convergent synthetic methodology. This molecule is ready for attachment to single-chain Fv antibodies (scFvs) to form antibody-multidrug immunoconjugates in an effort to study the relevance of drug/antibody molar ratio and the potency of these drug antibody immunoconjugates. A monomer and a trimer with a similar structural motif were also prepared for comparative purposes. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00361-x

文献信息

• Enabling ScFvs as multi-drug carriers: A dendritic approach
  作者：Chengzao Sun、Peter Wirsching、Kim D Janda

  DOI：10.1016/s0968-0896(03)00057-9

  日期：2003.4

  To enable scFvs as multi-drug carriers, we designed and synthesized dendritic linker molecules bearing up to nine chlorambucil residues at the branch ends. A maleimide group was used at the focal point of the dendron for easy linkage to the scFv. Originally designed molecules showed poor water solubility. To address this problem, a lysine residue with an unprotected carboxylic acid group was inserted into the dendron branches. The new molecules showed excellent water solubility and are now suitable for conjugation. Such dendritic molecules will allow studies to understand the relationship between the drug/antibody ratio and the potency of the immunoconjugates. The dendritic approach could also be applied to drugs other than chlorambucil and carriers other than scFvs to greatly increase the drug/carrier ratio. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Syntheses of dendritic linkers containing chlorambucil residues for the preparation of antibody–multidrug immunoconjugates
  作者：Chengzao Sun、Peter Wirsching、Kim D. Janda

  DOI：10.1016/s0960-894x(02)00361-x

  日期：2002.8

  A novel dendritic molecule with nine chlorambucil (CBL) residues on the surface and a maleimide moiety at the core terminus was synthesized using a convergent synthetic methodology. This molecule is ready for attachment to single-chain Fv antibodies (scFvs) to form antibody-multidrug immunoconjugates in an effort to study the relevance of drug/antibody molar ratio and the potency of these drug antibody immunoconjugates. A monomer and a trimer with a similar structural motif were also prepared for comparative purposes. (C) 2002 Elsevier Science Ltd. All rights reserved.